Simmondsin

Last updated

Simmondsin
Simmondsin.svg
Clinical data
ATC code
  • none
Identifiers
  • (2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H25NO9
Molar mass 375.374 g·mol−1
3D model (JSmol)
  • N#C\C=C2/[C@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C[C@H](OC)[C@H](OC)[C@H]2O
  • InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10-,11+,12-,13+,14-,15+,16-/m1/s1
  • Key:KURSRHBVYUACKS-XGYNEUJOSA-N
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Simmondsin is a component of jojoba seeds (pronounced "ho-HO-bah") ( Simmondsia chinensis ). While it had been considered toxic due to jojoba seed meal causing weight loss in animals, in recent years its appetite suppressant effect has also been researched as a potential treatment for obesity. [1] It is thought to reduce appetite by increasing levels of cholecystokinin. [2] [3] [4] [5]

References

  1. ↑ "Simmondsin From Jojoba - Checked for Appetite Suppression". United States Department of Agriculture, Agricultural Research Service.
  2. ↑ Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M (December 1995). "Devazepide reverses the anorexic effect of simmondsin in the rat". The Journal of Endocrinology. 147 (3): 473–7. doi:10.1677/joe.0.1470473. PMID   8543917.
  3. ↑ Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, et al. (August 1998). "Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats". Hormone and Metabolic Research. 30 (8): 504–8. doi:10.1055/s-2007-978921. PMID   9761380. S2CID   260166054.
  4. ↑ Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M (April 2000). "The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat". Appetite. 34 (2): 147–51. doi:10.1006/appe.1999.0299. PMID   10744903. S2CID   42949049.
  5. ↑ Boozer CN, Herron AJ (July 2006). "Simmondsin for weight loss in rats". International Journal of Obesity. 30 (7): 1143–8. doi:10.1038/sj.ijo.0803251. PMID   16462820. S2CID   1282460.
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